Boron tribromide → HCID 178465302, compound

HRID 1941967Notes

Reaction equation

HRID 1941967 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22]C)[N:17]=3)=[CH:14][C:13]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[N:17]=3)=[CH:14][C:13]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 578135901-Ethyl-3-[7-(6-methoxy-pyridin-2-yl)-5-pyridin-3-yl-benzothiazol-2-yl]-urea

Product 1

HCID 178465302HCID 178465302, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-ethyl-3-[7-(6-methoxy-pyridin-2-yl)-5-pyridin-3-yl-benzothiazol-2-yl]-urea (0.04 g, 0.098 mmol) in dry DCM was added BBr3 (0.50 ml) under nitrogen atmosphere at 0° C. The reaction mixture was then heated at 50° C. for 6 h under nitrogen atmosphere. Since the starting material was not consumed (TLC monitoring), toluene (5 mL) was added into the reaction mixture and heated at 120° C. for 16 h. After the completion of the reaction (TLC monitoring), the reaction mixture was cooled to 0° C. and quenched with ice-cold water. Toluene was distilled off, added water and extracted with DCM. The combined organic layers were dried over anhydrous Na2SO4, and evaporated to dryness under reduced pressure. The crude residue was purified over silica gel (100-200 M) using DCM-MeOH (96:4) to provide the title compound as off white solid (2.5 mg, 6%).

Workup

  1. customSince the starting material was not consumed (TLC monitoring), toluene (5 mL)
  2. additionwas added into the reaction mixture
  3. temperatureheated at 120° C. for 16 h
  4. customAfter the completion of the reaction (TLC monitoring)
  5. temperaturethe reaction mixture was cooled to 0° C.
  6. customquenched with ice-cold water
  7. distillationToluene was distilled off
  8. additionadded water
  9. extractionextracted with DCM
  10. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  11. customevaporated to dryness under reduced pressure
  12. customThe crude residue was purified over silica gel (100-200 M)

Sources & evidence

ORD record
ord-01c4991325bb436da5abc47036b72efe
Source dataset
uspto-grants-2013_03
Patent number
US08389516B2

Reaction notes

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